3-Deoxy-s-alkyl-d-glucose derivative micelle formation, CMC and thermodynamics

Bikanga, Raphaël; Bault, P.; Godé, P.; Ronco, G.; Villa, Pierre

doi:10.1007/bfb0115750

Cited by 8 publications

(8 citation statements)

References 6 publications

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“…During the past years, the carbohydrate chemistry literature has described a new range of amphiphilic compounds in which the polar head is either a hexose or an itol moiety linked to an alkyl chain (R = n-C n H 2n+1 ; n = 6-18) by an atom or functional group Z (Z = O, S, OCO) (1)(2)(3)(4)(5)(6)(7)(8)(9). These compounds were found to produce micelles and liquid crystals and to stabilize emulsions, while they exhibit a better biocompatibility (lower toxicity, higher biodegradability) than the usual nonionic surfactants such as sorbitan ester derivatives.…”

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confidence: 99%

Synthesis and surfactant properties of a new “extended” glucidoamphiphile made from D‐glucose

Scorzza

Godé

Martin

et al. 2002

J Surfact & Detergents

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We prepared a new nonionic surfactant, 8, in which the n-dodecyl chain is attached at the C-3 carbon of the D-glucose-based glucopyranose moiety by the linkage Z = -O-(α-PP-O) n with -O-(α-PP-O) n being a commercial poly-(αpropyloxy) oligomeric mixture (with average ñ = 6). This amphiphilic behavior study showed that, when compared to the reference compound 3-O-dodecyl-D-glucopyranose (Z = O), compound 8 exhibits (i) a water solubility that is 100-fold higher, (ii) a hydrophilic-lipophilic balance value increase from 8.5 to 12.6 units, and (iii) a slighly lower critical micelle concentration. SCHEME 2 a, Trityl (Tr) chloride (1.5 equiv), pyridine, reflux, 3 h (95%) 9; b, n-C 12 H 25 -Br (1.1 equiv), KOH (2.2 equiv), 4:1 toluene/dimethylsulfoxide (DMSO), room temperature (RT) 72 h (60%) 9; c, 4:1 AcOH/H 2 O, 100°C, 1 h 30 min (93%) 9; d, mesyl (Ms) chloride (1.1 equiv), 1:1 toluene/triethylamine, RT 72 h (60%); e, 6 (1.6 equiv), KOH (3.2 equiv), 4:1 toluene/DMSO, RT 72 h (52%); f, 9:1 CF 3 COOH/H 2 O, RT 30 min, twice (58%).

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confidence: 99%

Synthesis and surfactant properties of a new “extended” glucidoamphiphile made from D‐glucose

Scorzza

Godé

Martin

et al. 2002

J Surfact & Detergents

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“…D-Ribono derivatives have no CMC, due to the hydroxyl groups configuration. The other cyclic derivatives have, in general, surface activity and the CMC data are of the same order of magnitude for the same alkyl chain length: for arabinono-(5-8) and xylonolactone (9)(10)(11)(12) derivatives, it seems that the symmetric position of the hydroxyl groups versus cycle gives close values, the little differences proceeding the surrounding atoms. Thus molecular modelization of 5-S-hexyl-5-thio-D-pentono-1,4-1actones [17] gives: 2.…”

Section: Resultsmentioning

confidence: 84%

“…With regard to the amphiphilic behavior, it was shown that CMC of these compounds are mainly dependent on the following structural parameters: alkyl chain length [7][8][9][10][11][12], linkage Z [8,9,11,12], cyclic or acyclic structure of Su [8,10].…”

Section: Introductionmentioning

confidence: 99%

“…It was shown that glycoderivatives with the general formula Su-ZR, in which a hexose or alditolic unit Su is linked by an atom or an atom group Z = O, S, OCO to R alkyl chains (R = C n H 2n+1 ; n = 6-18), constitute a wide range of nonionic amphiphilic compounds, atoxic and biodegradable, studied in the last years [7][8][9][10][11][12]. With regard to the amphiphilic behavior, it was shown that CMC of these compounds are mainly dependent on the following structural parameters: alkyl chain length [7][8][9][10][11][12], linkage Z [8,9,11,12], cyclic or acyclic structure of Su [8,10].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and amphiphilic properties of S-alkylthiopentonolactones and their pentitol derivatives

Lalot

Stasik

Demailly

et al. 2004

Journal of Colloid and Interface Science

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“…Bikanga e colaboradores (BIKANGA et al, 1996) estudaram tensoativos sulfurados derivados da glucose (8 e 9). glucam) e, ao contrário da quitina, é solúvel em meio ácido, tornando mais fácil a obtenção de derivados (PETER, 1995;.…”

Section: Outros Tensoativos Não-comerciaisunclassified

Novos tensoativos derivados da 2-D-glucosamina

Bazito¹,

Seoud²

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AgradecimentosEm primeiro lugar e acima de tudo, agradeço a Deus pela minha existência e a de tudo e todos que me cercam.Ao Prof. Omar El Seoud pela orientação e oportunidade proporcionados nesses anos de convívio. Ao Prof. Frank H. Quina (IQ-USP), pelo auxílio nas medidas de fluorescência, e à Profa. Rosângela Itri (Instituto de Física -USP), pela realização das medidas e auxílio na interpretação dos resultados de espalhamento de raios X em baixo ângulo (SAXS).Ao Paulinho, por sua paciência oriental na realização dos experimentos de RMN e dos softwares "caseiros" que tanto agilizaram este trabalho.À Ellen Nogueira, pela ajuda nas medidas de espalhamento de luz e tensões superficiais.Ao pessoal da Central Analítica, da Biblioteca, da Secretaria de Pós-Graduação, do Setor Administrativo e de apoio do IQ-USP, pela paciência e pelo auxílio indispensáveis na realização deste trabalho.Ao CNPq, Capes, Finep e Fapesp, pelo auxílio financeiro proporcionado ao nosso laboratório e ao IQ-USP, sem o que seria impossível a realização deste trabalho.À Fapesp e à Capes, pela bolsa de doutoramento concedida.Ao pessoal do laboratório: Ana, Cesar, Dona Euzita, Erika, Naiara, Paulo, Ricardo, Susana, pelo saudável ambiente de trabalho, companheirismo, sugestões e discussões, ao longo de todo esse tempo.Aos amigos do IQ-USP (e ex-IQ-USP): Fabio, Guilherme, Marcia, Sascha, Shirley, e tantos outros, o meu agradecimento especial, pela amizade constante, apoio nos momentos difíceis, e pelas muitas e muitas risadas que tornaram tudo muito mais fácil. The anionic surfactants were obtained by the acylation of 2-Dglucosamine with acyl chlorides (with 8, 12 and 16 carbons), followed by the methylation of these derivatives with methanol in acidic media, and the sulfation of the methyl glucosides with sulfur trioxide-pyridine complex.The cationic surfactants were obtained by the tosylation of methyl glucosides followed by the quaternization with trimethylamine and exchange of the tosylate contra-ion with chloride ions on an ion exchange resin.These surfactants showed c.m.c. similar to other ionic surfactants with equal hydrophobic chain lengths, but more favorable free energies of transfer of the polar head to the micelle. This fact is attributed to hydrogen bonding between the head groups of the surfactant in the micelle, and the hydrophobicity of the sugar moiety.The micelles of these surfactants showed aggregation numbers larger than those obtained for other surfactants, problably because of head-group attractive interactions.Introdução 1 IntroduçãoOs tensoativos ou surfatantes são moléculas anfifílicas, isto é, que possuem duas regiões de polaridades diferentes: uma polar (ou hidrofílica) e outra apolar (ou hidrofóbica). Isso lhes confere uma grande capacidade de adsorção em interfaces, diminuindo as energias interfaciais, daí seu nome ("surfactant" = "surface active") (ROSEN, 1989 Os zwitteriônicos, devido ao seu baixo poder de irritação à pele e aos olhos, têm tido crescente aplicação em produtos para higiene pessoal (SMITH, 1979...

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3-Deoxy-s-alkyl-d-glucose derivative micelle formation, CMC and thermodynamics

Cited by 8 publications

References 6 publications

Synthesis and surfactant properties of a new “extended” glucidoamphiphile made from D‐glucose

Synthesis and surfactant properties of a new “extended” glucidoamphiphile made from D‐glucose

Synthesis and amphiphilic properties of S-alkylthiopentonolactones and their pentitol derivatives

Novos tensoativos derivados da 2-D-glucosamina

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